Organic compound, an electron transport material and an application thereof

ABSTRACT

The present disclosure provides an organic compound, an electron transport material, and an application thereof. The organic compound has a structure as shown in Formula I. Design of molecular structure and substituents enables it to undergo tridentate coordination or tetradentate coordination with metal, and more stably and firmly combination with metal, so that it has stronger stability and longer working life when used as an electron transport material, which effectively solves a problem of rising drift voltage. The organic compound has greater rigid distortion, which can suppress an increase of intermolecular attraction and prevent it from forming a planar structure to cause excessive intermolecular attraction. The organic compound is used as an electron transport material, and can be applied to an electron transport layer and/or an electron injection layer of an OLED device, which can effectively improve luminous efficiency and working life of the device, and reduce turn-on voltage.

CROSS-REFERENCE TO RELATED APPLICATIONS

The application claims the benefit of the earlier filing date of ChinesePatent Application No. 201911380047.4, filed on Dec. 27, 2019 to theChina National Intellectual Property Administration, the contents ofwhich are incorporated by reference herein in its entirety.

FIELD

The present disclosure belongs to the field of organicelectroluminescent materials, and in particular relates to an organiccompound, an electron transport material and an application thereof.

BACKGROUND

Organic electroluminescence technology is an emerging technology in thefield of optoelectronics. Organic Light Emitting Diodes (OLEDs) haveadvantages of self-luminous, wide viewing angles, ultra-thin, fastresponse, high luminous efficiency, good temperature adaptability,simple production process, low driving voltage, and low energyconsumption, compared to traditional inorganic electroluminescentdevices, and it has been widely used in industries such as flat paneldisplay, flexible display, solid-state lighting and on-board display Atpresent, OLEDs have entered industrialization stage. A growing demandfor display has driven rapid development of OLED devices and organicoptoelectronic materials. Specific manifestation is that compounds andmaterials with new structures, functional groups and substituents areconstantly emerging. At the same time, structure of OLED devices hasalso been continuously optimized, and has gradually developed from aninitial sandwich structure to a complex structure composed of multiplefunctional layers. Taking a classic organic electroluminescent device asan example, the laminated structure thereof includes a cathode, ananode, and an organic film layer between the cathode and the anode. Theorganic film layer includes a light emitting layer, an electrontransport layer, a hole transport layer, a hole injection layer and anelectron injection layer.

Electron transport materials commonly used in electron transport layersof OLEDs have the following characteristics: good film-formingproperties, higher electron affinity energy to facilitate electroninjection, higher electron mobility to facilitate electron transport,and good thermal stability Most of the electron transport materials arearomatic compounds and organometallic complexes with conjugate planes.They have a good ability to accept electrons, meanwhile, can effectivelytransfer electrons.

The earliest electron transport material used in OLED devices is8-hydroxyquinoline aluminum (Alq₃), which is a bidentate coordinatedchelate with a stable five-membered ring structure. Its thin films canbe prepared by vacuum evaporation. Electron mobility of Alq₃ isrelatively low, which is about 10⁻⁶ cm²/Vs, resulting in unbalancedelectron transport and hole transport of the device. With development ofOLED devices towards producibility and practicability, Alq₃ has beenunable to meet performance requirements of electroluminescent device.

Therefore, it is a research focus in this field to develop more kinds ofelectron transport materials.

SUMMARY

In order to develop more kinds of electron transport materials withhigher performance and more stably combining with metals, a first aspectof the present disclosure is to provide an organic compound, which has astructure as shown in Formula I:

In Formula I, m₁ and m₂ are each independently 0 or 1, and m₁+m₂≥1,i.e., m₁ and m₂ cannot be 0 at the same time.

In Formula I, U₁ and U₂ are each independently selected from any one ofthe following groups:

X₁, X₂ and X₃ are each independently selected from N or C—H.

Y₁ and Y₂ are each independently selected from O, S or N—R_(N).

R₁, R₂, R₃, R₄ and R₅ are each independently selected from any one ofhydrogen, deuterium, tritium, a silicon-containing substituent, a C1-C30straight or branched alkyl, a C1-C30 alkoxyl, a substituted orunsubstituted adamantyl, a substituted or unsubstituted C6-C40 aryl, anda substituted or unsubstituted C3-C40 heteroaryl.

When U₁ and U₂ are selected from

at least one of R₁, R₂, R₃ and R₄ is a silicon-containing substituent.

When any one of U₁ and U₂ is

at least one of R₁, R₂, R₃, R₄, and R₅ is a silicon-containingsubstituent.

R_(U) and R_(N) are each independently selected from any one ofhydrogen, deuterium, tritium, a C1-C30 straight or branched alkyl, aC1-C30 alkoxyl, a substituted or unsubstituted C6-C40 aryl, asubstituted or unsubstituted C3-C40 heteroaryl.

R₁₁ and R₁₂ are each independently selected from any one of hydrogen,deuterium, tritium, a C1-C30 straight or branched alkyl, a C1-C30alkoxyl, a substituted or unsubstituted C6-C40 aryl, and a substitutedor unsubstituted C3-C40 heteroaryl.

u₁, u₄ and u₆ are each independently selected from an integer of 0-4,for example 0, 1, 2, 3 or 4.

u₂ is selected from an integer of 0-6, for example 0, 1, 2, 3, 4, 5 or6.

u₃ and u₅ are each independently selected from an integer of 0-3, forexample 0, 1, 2, or 3.

In the above groups, the dotted line represents linking position of agroup.

The C1-C30 can be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C27 or C29.

The C6-C40 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C28, C30,C33, C35, C37 or C39.

The C3-C40 can be C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C28, C30, C33, C35, C37 or C39.

A second aspect of the present disclosure is to provide an electrontransport material comprising the organic compound according to thefirst aspect.

A third aspect of the present disclosure is to provide a display panel,and the display panel comprises an OLED device, the OLED devicecomprises an anode, a cathode, and an organic thin film layer betweenthe anode and the cathode, and the organic thin film layer comprises anelectron transport layer.

The material of the electron transport layer includes the electrontransport material according to the second aspect.

A fourth aspect of the present disclosure is to provide a display devicecomprising the display panel according to the third aspect.

Compared with the related technics, the present disclosure achieves thefollowing beneficial effects:

The organic compound provided by the present disclosure has a skeletalstructure of o-phenanthroline. Design of molecular structure andsubstituents of the present disclosure enables it to undergo tridentatecoordination or tetradentate coordination with a metal, realizing morestable and firm combination between the organic compound and the metal,so that it has stronger stability and longer working life when used asan electron transport material, which effectively solves the problem ofrising drift voltage. The organic compound will not absorb wavelengthsin visible light range, and its o-phenanthroline skeletal structurecoordinates with a large sterically hindered substituent mutually, whichgives the organic compound a large rigid distortion, suppressing anincrease of intermolecular attraction and being able to prevent it fromforming a planar structure to cause excessive intermolecular attraction.Since the organic compound provided by the present disclosure has a LUMOvalue of 1.4-2.0 eV, it is suitable to be used as common layer materialfor electron transport, which is used as an electron transport layerand/or an electron injection layer of an OLED device, and caneffectively improve luminous efficiency and working life of the device,and reduce turn-on voltage.

DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic structural diagram of an OLED device provided bythe present disclosure, and 101 is an anode, 102 is a cathode, 103 is alight emitting layer, 104 is a first organic thin film layer, and 105 isa second organic thin film layer.

DETAILED DESCRIPTION

The technical solutions of the present disclosure will be furtherdescribed below by way of specific embodiments. The embodiments aremerely illustrations of the present disclosure and should not beconstrued as specific limitations to the present disclosure.

One aspect of the present disclosure is to provide a compound having astructure as shown in Formula I:

In Formula I, m₁ and m₂ are each independently 0 or 1, and m₁+m₂≥1,i.e., m₁ and m₂ cannot be 0 at the same time.

In Formula I, U₁ and U₂ are each independently selected from any one ofthe following groups:

X₁, X₂ and X₃ are each independently selected from N or C—H.

Y₁ and Y₂ are each independently selected from O, S or N—R_(N).

R₁, R₂, R₃, R₄ and R₅ are each independently selected from any one ofhydrogen, deuterium, tritium, a silicon-containing substituent, a C1-C30straight or branched alkyl, a C1-C30 alkoxyl, a substituted orunsubstituted adamantyl, a substituted or unsubstituted C6-C40 aryl, anda substituted or unsubstituted C3-C40 heteroaryl.

When U₁ and U₂ are selected from

at least one of R₁, R₂, R₃ and R₄ is a silicon-containing substituent.

When any one of U₁ and U₂ is

at least one of R₁, R₂, R₃, R₄, and R₅ is a silicon-containingsubstituent.

R_(U) and R_(N) are each independently selected from any one ofhydrogen, deuterium, tritium, a C1-C30 straight or branched alkyl, aC1-C30 alkoxyl, a substituted or unsubstituted C6-C40 aryl, and asubstituted or unsubstituted C3-C40 heteroaryl.

R₁₁ and R₁₂ are each independently selected from any one of hydrogen,deuterium, tritium, a C1-C30 straight or branched alkyl, a C1-C30alkoxyl, a substituted or unsubstituted C6-C40 aryl, and a substitutedor unsubstituted C3-C40 heteroaryl.

u₁, u₄ and u₆ are each independently selected from an integer of 0-4,for example 0, 1, 2, 3 or 4.

u₂ is selected from an integer of 0-6, for example 0, 1, 2, 3, 4, 5 or6.

u₃ and u₅ are each independently selected from an integer of 0-3, forexample 0, 1, 2, or 3.

In the above groups, the dotted line represents linking position of agroup.

The C1-C30 can be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C27 or C29.

The C6-C40 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C28, C30,C33, C35, C37 or C39.

The C3-C40 can be C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C28, C30, C33, C35, C37 or C39.

The organic compound provided by the present disclosure has ao-phenanthroline skeletal structure, and the skeletal structure includesat least one substituent (U₁ and/or U₂) containing non-shared electronpairs. When m₁+m₂=1, the organic compound contains three non-sharedelectron pairs, which can be combined with a metal through coordinationbonds to form a stable tridentate coordination structure; and whenm₁+m₂=2, the organic compound contains four non-shared electron pairs,which can be combined with a metal through coordination bonds to form astable tetradentate coordination structure. The organic compoundprovided by the present disclosure effectively improves firmness andbonding stability of combination with a metal by forming a tridentate ortetradentate coordination structure with the metal, which can suppressmetal movement caused by heat and electric field generated during devicedriving process and avoids electron injection and movementcharacteristics caused by changes in arrangement of an electrontransport layer in early stage of driving, and finally improves workinglife of a OLED device.

In the organic compound provided by the present disclosure, theo-phenanthroline skeletal structure and a plurality of large stericallyhindered substituents cooperate with each other, so that the organiccompound has a large rigid distortion, and avoids increase inintermolecular attraction caused by excessive planar structure of aconventional phenanthroline compound. The organic compound has asuitable spatial structure and molecular weight, and its molecularweight is in the range of 600-1200 g/mol, which is helpful forcontrolling evaporation rate and can suppress accumulation caused byincrease in intermolecular attraction.

In one embodiment, substituent in a substituted aryl and substitutedheteroaryl is selected from at least one of the group consisting ofdeuterium, tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9)straight or branched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12,C14, C15, C17 or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16or C18) heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9)alkoxyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19)arylamino, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)cycloalkyl, and halogen (e.g., fluorine, chlorine, bromine or iodine).

In one embodiment, R₁, R₂, R₃, R₄ and R₅ are each independently selectedfrom any one of the group consisting of hydrogen, deuterium, tritium, asilicon-containing substituent, a substituted or unsubstituted C6-C20(e.g., C7, C9, C10, C12, C14, C15, C17 or C19) aryl, and a substitutedor unsubstituted C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl.

When U₁ and U₂ are selected from

at least one of R₁, R₂, R₃ and R₄ is a silicon-containing substituent.

When any one of U₁ and U₂ is

at least one of R₁, R₂, R₃, R₄, and R₅ is a silicon-containingsubstituent.

When a substituent is present in the above group, the substituent isselected from at least one of the group consisting of deuterium,tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9) straight orbranched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxyl,C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19) arylamino, C3-C20(e.g., C4, C6, C8, C10, C12, C14, C16 or C18) cycloalkyl, and halogen(e.g., fluorine, chlorine, bromine or iodine).

In one embodiment, U₁ and U₂ are each independently selected from anyone of the following groups:

In one embodiment, each of R₄, R₅, R_(U), R_(N), R₁₁, R₁₂, u₁, u₂, u₃,u₄, u₅, and u₆ independently has the same limited range as that inFormula 1.

u₁₁ is an integer of 0-2, for example 0, 1 or 2.

The dotted line represents linking position of a group.

In one embodiment, U₁ and U₂ are each independently selected from anyone of the following groups:

In one embodiment, the dotted line represents linking position of agroup.

In one embodiment, the organic compound has a structure as shown in anyone of Formula I-1 to Formula I-4:

In one embodiment, each of X₁, X₂, Y₁, Y₂, R_(U), R₁₁, R₁₂, u₁, u₂, u₃,u₄, u₅, and u₆ independently has the same limited range as that inFormula I.

R₁, R₂, R₃, R₄ and R₅ are each independently selected from any one ofhydrogen, deuterium, tritium, a silicon-containing substituent, a C1-C30straight or branched alkyl, a C1-C30 alkoxyl, a substituted orunsubstituted C6-C40 aryl, and a substituted or unsubstituted C3-C40heteroaryl.

The C1-C30 can be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C27 or C29.

The C6-C40 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C28, C30,C33, C35, C37 or C39.

The C3-C40 can be C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C28, C30, C33, C35, C37 or C39.

In Formula I-1 and Formula I-2, at least one of R₁, R₂, R₃, and R₄ is asilicon-containing substituent.

In Formula I-3 and Formula I-4, at least one of R₁, R₂, R₃, R₄, and R₅is a silicon-containing substituent.

When a substituent is present in the above group, the substituent isselected from at least one of the group consisting of deuterium,tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9) straight orbranched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxyl,C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19) arylamino, C3-C20(e.g., C4, C6, C8, C10, C12, C14, C16 or C18) cycloalkyl, and halogen(e.g., fluorine, chlorine, bromine or iodine).

When the organic compound according to the present disclosure has astructure as shown in any one of Formula I-1 to Formula I-4, themolecular structure contains three non-shared electron pairs, and whenit is used as an electron transport material, it can form a stablestructure of tridentate coordination with a metal.

In one embodiment, the organic compound has a structure as shown in anyone of Formula I-5 to Formula I-11:

In one embodiment, each of X₁, X₂, Y₁, Y₂, R_(U), R₁₁, R₁₂, and u₁independently has the same limited range as that in Formula I.

R₁, R₂, R₃, R₄ and R₅ are each independently selected from any one ofhydrogen, deuterium, tritium, a silicon-containing substituent, a C1-C30straight or branched alkyl, a C1-C30 alkoxyl, a substituted orunsubstituted C6-C40 aryl, and a substituted or unsubstituted C3-C40heteroaryl.

The C1-C30 can be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C27 or C29.

The C6-C40 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C28, C30,C33, C35, C37 or C39.

The C3-C40 can be C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C28, C30, C33, C35, C37 or C39.

In Formula I-5, Formula I-6, and Formula I-9, at least one of R₁, R₂,R₃, and R₄ is a silicon-containing substituent.

In Formula I-7, Formula I-8, Formula I-10, and Formula I-11, at leastone of R₁, R₂, R₃, R₄, and R₅ is a silicon-containing substituent.

When a substituent is present in the above group, the substituent isselected from at least one of the group consisting of deuterium,tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9) straight orbranched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxyl,C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19) arylamino, C3-C20(e.g., C4, C6, C8, C10, C12, C14, C16 or C18) cycloalkyl, and halogen(e.g., fluorine, chlorine, bromine or iodine).

When the organic compound according to the present disclosure has astructure as shown in any one of Formula I-5 to Formula I-11, themolecular structure contains four non-shared electron pairs, and when itis used as an electron transport material, it can form a stablestructure of tetradentate coordination with a metal.

In one embodiment, at least one of R₁, R₂, and R₃ is asilicon-containing substituent.

In one embodiment, at least one of R₁ and R₃ is a silicon-containingsubstituent.

In one embodiment, the silicon-containing substituent has a structure asshown in Formula II:

In Formula II, Ar is selected from a single bond, a substituted orunsubstituted C6-C30 arylene group.

In Formula II, R_(S1), R_(S2) and R_(S3) are each independently selectedfrom any one of a C1-C30 straight or branched alkyl, a C1-C30 alkoxyl, asubstituted or unsubstituted C6-C40 aryl, and a substituted orunsubstituted C3-C40 heteroaryl.

The C6-C30 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C27 or C29.

The C1-C30 can be C2, C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C27 or C29.

The C6-C40 can be C7, C8, C10, C13, C15, C18, C20, C23, C25, C28, C30,C33, C35, C37 or C39.

The C3-C40 can be C4, C5, C6, C8, C10, C13, C15, C18, C20, C23, C25,C28, C30, C33, C35, C37 or C39

In Formula II, the dotted line represents linking position of a group.

When a substituent is present in the above group, the substituent isselected from at least one of the group consisting of deuterium,tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9) straight orbranched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxyl,C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19) arylamino, C3-C20(e.g., C4, C6, C8, C10, C12, C14, C16 or C18) cycloalkyl, and halogen(e.g., fluorine, chlorine, bromine or iodine).

In one embodiment, Ar is selected from a single bond or a C6-C20 (forexample, C7, C9, C10, C12, C14, C15, C17 or C19) arylene group.

In one embodiment, R_(S1), R_(S2) and R_(S3) are each independentlyselected from any one of the group consisting of a substituted orunsubstituted C6-C40 (for example, C7, C8, C10, C13, C15, C18, C20, C23,C25, C28, C30, C33, C35, C37 or C39) aryl group, a substituted orunsubstituted C3-C40 (for example, C4, C5, C6, C8, C10, C13, C15, C18,C20, C23, C25, C28, C30, C33, C35, C37 or C39) heteroaryl group.

When a substituent is present in the above group, the substituent isselected from at least one of the group consisting of deuterium,tritium, C1-C10 (i.e., C2, C3, C4, C5, C6, C7, C8 or C9) straight orbranched alkyl, adamantyl, C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17or C19) aryl, C3-C20 (e.g., C4, C6, C8, C10, C12, C14, C16 or C18)heteroaryl, C1-C10 (e.g., C2, C3, C4, C5, C6, C7, C8 or C9) alkoxyl,C6-C20 (e.g., C7, C9, C10, C12, C14, C15, C17 or C19) arylamino, C3-C20(e.g., C4, C6, C8, C10, C12, C14, C16 or C18) cycloalkyl, and halogen(e.g., fluorine, chlorine, bromine or iodine).

In one embodiment, the silicon-containing substituent is selected fromany one of the following groups:

In one embodiment, the dotted line represents linking position of agroup.

In one embodiment, the organic compound is selected from any one of thefollowing compounds M1 to M41:

A second aspect of the present disclosure is to provide an electrontransport material comprising the organic compound as described above.

In one embodiment, the electron transport material is an electrontransport material containing a metal; and the metal is selected fromany one or a combination of at least two of an alkali metal, an alkalimetal compound, an alkaline earth metal, an alkaline earth metalcompound, a transition metal, a transition metal compound, a rare earthmetal, and a rare earth metal compound.

In the electron transport material, the organic compound provided by thepresent disclosure forms a stable structure of tridentate coordinationor a tetradentate coordination with a metal and/or a metal compound; andthe alkali metal includes Li, Na, K, Rb or Cs, the alkaline earth metalincludes Be, Mg, Ca, Sr or Ba, the transition metal includes Ti, Cr, Mn,Fe, Co, Ni, Zr, Nb, Mo, Ru, Rh, Pd, La, Hf, Re, Os, Ir or Pt, and therare earth metal includes La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho,Er, Tm, Yb or Lu.

A third aspect of the present disclosure is to provide a display panel,and the display panel comprises an OLED device, the OLED devicecomprises an anode, a cathode, and an organic thin film layer betweenthe anode and the cathode, the organic thin film layer includes anelectron transport layer; the material of the electron transport layerincludes the electron transport material as described above.

In one embodiment, the organic thin film layer further comprises anelectron injection layer; material of the electron injection layerincludes the electron transport material as described above.

In the OLED device according to the present disclosure, anode materialmay be a metal, a metal oxide or a conductive polymer; and the metalincludes copper, gold, silver, iron, chromium, nickel, manganese,palladium, platinum, or the alloys thereof, the metal oxide includesindium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide, or indiumgallium zinc oxide (IGZO), and the conductive polymer includespolyaniline, polypyrrole, or poly (3-methylthiophene). In addition tothe materials and combination thereof as described above whichfacilitate hole injection, other materials known to be suitable foranodes can be included.

In the OLED device, the cathode material may be a metal or a multilayermetal material; and the metal includes aluminum, magnesium, silver,indium, tin, titanium and alloys thereof, and the multilayer metalmaterial includes LiF/Al, LiO₂/Al, and BaF₂/Al In addition to thematerials and combination thereof as described above which facilitateelectron injection, other materials known to be suitable for cathodescan be included.

In the OLED device, the organic thin film layer includes at least onelight emitting layer (EML) and any one or a combination of at least twoof an electron transport layer (ETL), a hole transport layer (HTL), ahole injection layer (HIL), an electron blocking layer (EBL), a holeblocking layer (HBL), and an electron injection layer (EIL) disposed onboth sides of the light emitting layer; and the hole injection andtransport layer may be a carbazole compound, an arylamine compound, anacridine compound, and the electron injection material or the transportmaterial includes a nitrogen-containing heterocyclic compound, aboron-containing heterocyclic compound, a phosphorus-containingcompound, a fused aromatic ring compound and a metal compound.

A schematic diagram of the OLED device is as shown in FIG. 1 andincludes an anode 101 and a cathode 102, a light emitting layer 103disposed between the anode 101 and the cathode 102, a first organic thinfilm layer 104 and a second organic thin film layer 105 are provided onboth sides of the light emitting layer 103, the first organic thin filmlayer 104 is any one or a combination of at least two of a holetransport layer (HTL), a hole injection layer (HIL), or an electronblocking layer (EBL), the second organic thin film layer 105 is anelectron transport layer (ETL), and the second organic thin film layer105 further includes a hole blocking layer (HBL) and/or an electroninjection layer (EIL).

The OLED device can be prepared by the following method: forming ananode on a transparent or non-transparent smooth substrate, forming anorganic thin layer on the anode, and forming a cathode on the organicthin layer. In one embodiment, the organic thin layer can be formed byknown film-forming methods such as evaporation, sputtering, spincoating, dipping, and ion plating

A fourth aspect of the present disclosure is to provide a display devicecomprising the display panel according to the third aspect.

The organic compounds provided by the present disclosure are exemplarilyprepared by the following synthetic route:

In the above synthetic route, the benzopyridine compound A undergoes aone-step nitration reaction to obtain a nitration product B; thenitration product B undergoes a cycloaddition reaction with a terminalalkyne-containing compound to obtain a fused ring product C; and thefused ring product C undergoes a hydrolysis reaction to obtain acompound D; the compound D is cyclized with a methyl ketone compoundcontaining a U₂ substituent to obtain the core structure E of GeneralFormula I; when X is a halogen, the core structure E undergoes acoupling reaction with

under the catalysis of palladium catalyst to obtain

In the above synthetic route, X represents hydrogen, halogen (e.g.,chlorine or bromine) or U₁, each of R₁, R₂, R₃, U₁, and U₂ independentlyhas the same limited range as that in Formula I.

The organic compounds provided by the present disclosure can be preparedthrough selection of different raw materials based on the abovesynthetic route.

Example 1

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M16 includes the followingsteps:

In a 100 mL three-necked flask, first dissolving S1 (10 mmol, where TMSis trimethylsilyl) in 20 mL of concentrated sulfuric acid, andcontrolling the temperature in an ice-water bath. After stirring evenlyat a certain rotation speed, adding concentrated nitric acid (15 mmol)to the reaction system for 2 h; adjusting the reaction solution toneutrality with an aqueous NaOH solution under an ice water bath; afterthe reaction was completed, extracting the reaction system with diethylether, and drying the obtained organic phase over anhydrous sodiumsulfate, distilling off the solvent and purifying through columnchromatography to obtain intermediate S2 (9.5 mmol, yield 95%).

The structure of intermediate S2 was tested: MALDI-TOF-MS (m/z) obtainedby Matrix assisted laser desorption ionization time-of-flight massspectrometry: C₁₂H₁₃N₂O₂, calculated value: 280.78, tested value:280.04.

Under the protection of nitrogen, dissolving intermediates S2 (1 mmol)and S3 (1.2 mmol) in 20 mL of toluene, addingtetra(triphenylphosphine)palladium Pd(PPh₃)₄ (0.05 mmol) as a catalyst,and adding 2 mL of aqueous potassium carbonate solution (2 mol/L),refluxing the same for 12 h; after the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatethree times, combining the organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting the crude product. Purifying the crude product by asilica gel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain intermediate S6 (0.87 mmol, yield 87%).

The structure of intermediate S4 was tested: MALDI-TOF-MS (m/z) obtainedby Matrix assisted laser desorption ionization time-of-flight massspectrometry: C₁₇H₁₇N₃O₂Si, calculated value: 323.42, tested value:323.11.

Under the protection of nitrogen, dissolving intermediates S4 (3 mmol)and S5 (3.1 mmol) in 20 mL of tetrahydrofuran (THF), reducing thetemperature to −60° C. with an ethanol bath, and dropwise adding 3.3mmol of potassium tert-butoxide (t-BuOK) dissolved in 5 mL of THF to thereaction system; after 5 min, adding 12 mmol of trimethylchlorosilaneMe₃SiCl, and stirring continuously at low temperature for 5 min; thendissolving 15 mmol of t-BuOK in 20 mL of THF solution, and injecting thesame to the reaction system. Naturally returning the reaction system toroom temperature, and stirring continuously for 3.5 h. After thereaction was completed, pouring the reaction solution into a dilutehydrochloric acid solution and extracted with ethyl acetate severaltimes, combining the organic phases, and then drying the same overanhydrous Na₂SO₄. Removing all solvents by reduced pressuredistillation, and collecting the crude product. Purifying the crudeproduct by a silica gel column chromatography using a mixed solvent ofn-hexane and chloroform in a volume ratio of 5:1 as an eluent, andfinally purifying to obtain solid intermediate S6 (2.73 mmol, yield91%).

The structure of intermediate S6 was tested: MALDI-TOF-MS (m/z) obtainedby Matrix assisted laser desorption ionization time-of-flight massspectrometry: C₂₄H₂₁N₃OSi, calculated value: 395.53, tested value:395.15.

Charging intermediate S6 (1 mmol), triethylamine (1 mL), palladium oncarbon (10%, 10 mg) and 6 mL of tetrahydrofuran (THF) in a reactionkettle. Injecting hydrogen into the reaction kettle to bring thepressure in the reaction kettle to 10 bar. Stirring the reaction systemat room temperature for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor several times, combining the organic phases, and then drying thesame over Na₂SO₄. Removing all solvents by reduced pressuredistillation, and collecting a crude product. Purifying the crudeproduct by a silica gel column chromatography using a mixed solvent ofn-hexane and chloroform in a volume ratio of 5:1 as an eluent, andfinally purifying to obtain intermediate S7 (0.95 mmol, yield 95%).

The structure of the intermediate S7 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₄H₂₃N₃OSi, calculated value: 397.54, tested value:397.16.

Placing intermediates S7 (1 mmol), S8 (1.05 mmol) and diamyl phthalate(DPP, 0.5 mmol) in a microwave reactor and subjecting the same tomicrowave reaction for 3 min. After the reaction was completed, dilutingthe reaction system with ethyl acetate, neutralizing with a 10% aqueousNaOH solution, and extracting with ethyl acetate, drying the organicphase over Na₂SO₄. Purifying the crude product through a silica gelchromatography column using a mixed solvent of ethyl acetate andn-hexane in a volume ratio of 1:20 as an eluent, and finally purifyingto obtain a solid intermediate S9 (0.74 mmol, yield 74%).

The structure of intermediate S9 was tested: MALDI-TOF-MS (m/z) obtainedby Matrix assisted laser desorption ionization time-of-flight massspectrometry: C₃₁H₂₆N₄Si, calculated value: 482.65, tested value:482.19.

Under protection of nitrogen, dissolving intermediate S9 (1 mmol) andN-bromosuccinimide (NBS, 1.5 mmol) in 50 mL of chloroform, and stirringthe same at room temperature for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting crude product. Purifying the crude product by a silicagel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain intermediate S10 (0.97 mmol, yield 97%).

The structure of intermediate S10 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₈H₁₇BrN₄, calculated value: 489.37, tested value:488.06.

Under protection of nitrogen, dissolving intermediates S10 (1 mmol) andS11 (1.1 mmol) in toluene, adding Pd(PPh₃)₄ (0.05 mmol) as a catalyst,and adding 2 mL of aqueous potassium carbonate solution (2 mol/L),refluxing the same for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting crude product. Purifying the crude product by a silicagel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain the solid desired product M16 (0.89 mmol, yield 89%).

The structure of the desired product M16 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₅₂H₃₆N₄Si, calculated value: 744.95, tested value:744.27.

Elemental analysis: Theoretical value: C 83.84, H 4.87, N 7.52, Si 3.77;tested value: C 83.85, H 4.85, N 7.56, Si 3.74.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 2H), 7.22 (m, 1H), 7.32 (m,2H), 7.36 (m, 9H), 7.43 (m, 1H), 7.48 (m, 2H), 7.54 (m, 6H), 7.58-7.60(m, 4H), 7.66-7.68 (m, 3H), 8.50 (m, 2H), 8.59-8.62 (m, 4H).

Example 2

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M19 includes the followingsteps:

obtaining intermediate S10 according to the method of steps (1) to (6)in Example 1;

Adding intermediate S10 (1 mmol) and tetramethylethylenediamine (2.5mmol) to 90 mL of THF, reducing the temperature to −78° C. in an ethanolbath, and dropwise adding tert-butyllithium (t-BuLi, 2.5 mmol) into thereaction system within 15 min, and stirring at low temperature for 1 h.Adding S12 (2.5 mmol) at low temperature, and after stirring at lowtemperature for 1 h, naturally returning it to room temperature andstirring overnight. After the reaction was completed, extracting thereaction system with water and ethyl acetate, and then drying organicphase over Na₂SO₄. Purifying the crude product by a silica gel columnchromatography using a mixed solvent of n-hexane and chloroform in avolume ratio of 5:1 as an eluent, and finally purifying to obtain thesolid desired product M19 (0.87 mmol, yield 87%).

The structure of the desired product M19 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₄₆H₃₂N₄Si, calculated value: 668.86, tested value:668.24.

Elemental analysis: Theoretical value: C 82.60, H 4.82, N 8.38, Si 4.20;tested value: C 82.62, H 4.81, N 8.38, Si 4.21.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 2H), 7.22 (m, 1H), 7.32 (m,2H), 7.36 (m, 9H), 7.43 (m, 1H), 7.48 (m, 2H), 7.54 (m, 6H), 7.66-7.68(m, 3H), 8.50 (m, 2H), 8.59-8.60 (m, 3H), 8.66 (s, 1H).

Example 3

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M2 includes the followingsteps:

obtaining intermediate S10 according to the method of steps (1) to (6)in Example 1;

Under protection of nitrogen, dissolving intermediates S10 (2 mmol) andS13 (1 mmol) in 30 mL of toluene, adding Pd(PPh₃)₄ (0.1 mmol) as acatalyst, and adding 4 mL of aqueous potassium carbonate solution (2mol/L), refluxing the same for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining the organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting a crude product. Purifying the crude product by a silicagel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:2 as an eluent, and finally purifyingto obtain a solid desired product M2 (0.80 mmol, yield 80%).

The structure of the desired product M2 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₈₀H₅₂N₈Si, calculated value: 1153.41, tested value:1152.41.

Elemental analysis: Theoretical value: C 83.31, H 4.54, N 9.72, Si 2.44;tested value: C 83.30, H 4.53, N 9.73, Si 2.45.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 4H), 7.22 (m, 2H), 7.32 (m,4H), 7.36 (m, 6H), 7.42-7.43 (m, 4H), 7.48-7.50 (m, 6H), 7.54 (m, 4H),7.58 (m, 2H), 7.66-7.68 (m, 6H), 7.76 (m, 2H), 8.50 (m, 4H), 8.59-8.62(m, 8H).

Example 4

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M11 includes the followingsteps:

obtaining intermediate S4 according to the method of steps (1) to (2) inExample 1;

Under protection of nitrogen, dissolving intermediates S4 (3 mmol) andS14 (3.1 mmol) in 20 mL of tetrahydrofuran (THF), reducing itstemperature to −60° C. with an ethanol bath, and dropwise adding 3.3mmol of potassium tert-butoxide (t-BuOK) dissolved in 5 mL of THF to thereaction system; after 5 min, adding 12 mmol of Me₃SiCl, and stirringcontinuously at low temperature for 5 min. Then, dissolving 15 mmol oft-BuOK in 20 mL of THF solution, and injecting the same to the reactionsystem. Naturally returning the reaction system to room temperature, andstirring continuously for 3.5 h. After the reaction was completed,pouring the reaction solution into a dilute hydrochloric acid solutionand extracted with ethyl acetate for several times, combining theorganic phases, and then drying the same over Na₂SO₄. Removing allsolvents by reduced pressure distillation, and collecting a crudeproduct. Purifying the crude product by a silica gel columnchromatography using a mixed solvent of n-hexane and chloroform in avolume ratio of 5:1 as an eluent, and finally purifying to obtainintermediate S15 (2.58 mmol, yield 86%).

The structure of intermediate S15 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₁H₂₅N₃OSi₂, calculated value: 391.61, tested value:391.15.

Charging intermediate S15 (1 mmol), triethylamine (1 mL), palladium oncarbon (10%, 10 mg) and 6 mL of tetrahydrofuran (THF) in a reactionkettle. Injecting hydrogen into the reaction kettle to bring thepressure in the reaction kettle to 10 bar. Stirring the reaction systemat room temperature for 12 h. After the reaction was completed,extracting the reaction system with ethyl acetate for several times,combining the organic phases, and then drying the same over Na₂SO₄.Removing all solvents by reduced pressure distillation, and collectingthe crude product. Purifying the crude product by a silica gel columnchromatography using a mixed solvent of n-hexane and chloroform in avolume ratio of 5:1 as an eluent, and finally purifying to obtainintermediate S16 (0.90 mmol, yield 90%).

The structure of intermediate S16 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₁H₂₇N₃OSi₂, calculated value: 393.63, tested value:393.17.

Placing intermediates S16 (1 mmol), S8 (1.05 mmol) and diamyl phthalate(DPP, 0.5 mmol) in a microwave reactor and subjecting the same tomicrowave reaction for 3 min. After the reaction was completed, dilutingthe reaction system with ethyl acetate, and neutralizing with a 10%aqueous NaOH solution. Then extracting with ethyl acetate, and dryingthe organic phase over Na₂SO₄. Purifying the crude product through asilica gel chromatography column using a mixed solvent of ethyl acetateand n-hexane in a volume ratio of 1:20 as an eluent, and finallypurifying to obtain a solid intermediate S17 (0.71 mmol, yield 71%).

The structure of intermediate S17 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₈H₃₀N₄Si₂, calculated value: 478.74, tested value:478.20.

Under protection of nitrogen, dissolving intermediate S17 (1 mmol) andN-bromosuccinimide (NBS, 3 mmol) in 50 mL of chloroform, and stirringthe same at room temperature for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining the organic phases, drying over anhydroussodium sulfate, removing all solvents by reduced pressure distillation,and collecting a crude product. Purifying the crude product by a silicagel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain intermediate S18 (0.94 mmol, yield 94%).

The structure of intermediate S18 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₂H₁₂Br₂N₄, calculated value: 492.17, tested value:491.94.

Adding intermediate S18 (1 mmol) and tetramethylethylenediamine (2.5mmol) to 90 mL of THF, reducing the temperature to −78° C. in an ethanolbath, and dropwise adding tert-butyllithium (t-BuLi, 2.5 mmol) into thereaction system within 15 min, and stirring at low temperature for 1 h.Adding S12 (5 mmol) at low temperature, and after stirring at lowtemperature for 1 h, naturally returning it to room temperature andstirring overnight. After the reaction was completed, extracting thereaction system with water and ethyl acetate, and then drying theorganic phase over Na₂SO₄ to obtain a crude product. Purifying the crudeproduct by a silica gel column chromatography using a mixed solvent ofn-hexane and chloroform in a volume ratio of 5:1 as an eluent, andfinally purifying to obtain a solid desired product M11 (0.77 mmol,yield 77%).

The structure of the desired product M11 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₅₈H₄₂N₄Si₂, calculated value: 851.15, tested value:850.29.

Elemental analysis: Theoretical value: C 81.84, H 4.97, N 6.58, Si 6.60;tested value: C 81.85, H 4.96, N 6.59, Si 6.59.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 2H), 7.36 (m, 18H), 7.54 (m,4H), 7.66 (m, 2H), 8.50 (m, 2H), 8.59 (m, 2H), 8.66 (s, 2H).

Example 5

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M17 includes the followingsteps:

In a 100 mL three-necked flask, first dissolving S19 (10 mmol) in 20 mLof concentrated sulfuric acid, and controlling the temperature in anice-water bath. After stirring evenly at a certain rotation speed,adding concentrated nitric acid (15 mmol) to the reaction system for 2h; adjusting the reaction solution to neutrality with an aqueous NaOHsolution under an ice water bath; after the reaction was completed,extracting the reaction system with diethyl ether, and drying theobtained organic phase over anhydrous sodium sulfate, distilling off thesolvent and purifying through column chromatography to obtainintermediate S20 (9.0 mmol, yield 90%).

The structure of intermediate S20 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₁₂H₁₄N₂O₂Si, calculated value: 246.34, tested value:246.08.

Under protection of nitrogen, dissolving intermediates S20 (3 mmol) andS5 (3 mmol) in 20 mL of THF, reducing the temperature to −60° C. with anethanol bath, and dropwise adding 3.3 mmol of potassium tert-butoxide(t-BuOK) dissolved in 5 mL of THF to the reaction system; after 5 min,adding 12 mmol of trimethylchlorosilane Me₃SiCl, and stirringcontinuously at low temperature for 5 min; then dissolving 15 mmol oft-BuOK in 20 mL of THF solution, and injecting the same to the reactionsystem. Naturally returning the reaction system to room temperature, andstirring continuously for 3.5 h. After the reaction was completed,pouring the reaction solution into a dilute hydrochloric acid solutionand extracted with ethyl acetate for several times, combining organicphases, and then drying the same over Na₂SO₄. Removing all solvents byreduced pressure distillation, and collecting a crude product. Purifyingthe crude product by a silica gel column chromatography using a mixedsolvent of n-hexane and chloroform in a volume ratio of 5:1 as aneluent, and finally purifying to obtain intermediate S21 (2.37 mmol,yield 79%).

The structure of intermediate S21 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₁₉H₁₈N₂OSi, calculated value: 318.44, tested value:318.12.

Charging intermediate S21 (1 mmol), triethylamine (1 mL), palladium oncarbon (10%, 10 mg) and 6 mL of tetrahydrofuran (THF) in a reactionkettle. Injecting hydrogen into the reaction kettle to bring thepressure in the reaction kettle to 10 bar. Stirring the reaction systemat room temperature for 12 h. After the reaction was completed,extracting the reaction system with ethyl acetate for several times,combining organic phases, and then drying the same over Na₂SO₄. Removingall solvents by reduced pressure distillation, and collecting a crudeproduct. Purifying the crude product by a silica gel columnchromatography using a mixed solvent of n-hexane and chloroform in avolume ratio of 5:1 as an eluent, and finally purifying to obtainintermediate S22 (0.88 mmol, yield 88%).

The structure of intermediate S22 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₁₉H₂₀N₂OSi, calculated value: 320.46, tested value:320.13.

Placing intermediates S22 (1 mmol), S8 (1.1 mmol) and diamyl phthalate(DPP, 0.5 mmol) in a microwave reactor and subjecting the same tomicrowave reaction for 3 min. After the reaction was completed, dilutingthe reaction system with ethyl acetate, neutralizing with a 10% aqueousNaOH solution, and extracting with ethyl acetate, drying the organicphase over Na₂SO₄. Purifying the crude product through a silica gelchromatography column using a mixed solvent of ethyl acetate andn-hexane in a volume ratio of 1:20 as an eluent, and finally purifyingto obtain a solid intermediate S23 (0.68 mmol, yield 68%).

The structure of the intermediate S23 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₂₆H₂₃N₃Si, calculated value: 405.57, tested value:405.17.

Under protection of nitrogen, dissolving intermediate S23 (1 mmol) andN-bromosuccinimide (NBS, 1.5 mmol) in 50 mL of chloroform, and stirringthe same at room temperature for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining the organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting the crude product. Purifying the crude product by asilica gel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain intermediate S24 (0.92 mmol, yield 92%).

The structure of intermediate S24 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C23H₁₄BrN₃, calculated value: 412.28, tested value:413.04.

Under protection of nitrogen, dissolving intermediates S24 (1 mmol) andS11 (1.06 mmol) in 20 mL of toluene, adding Pd(PPh₃)₄ (0.05 mmol) as acatalyst, and adding 2 mL of aqueous potassium carbonate solution (2mol/L), refluxing the same for 12 h. After the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, combining the organic phases and drying over anhydroussodium sulfate. Removing all solvents by reduced pressure distillation,and collecting a crude product. Purifying the crude product by a silicagel column chromatography using a mixed solvent of n-hexane andchloroform in a volume ratio of 5:1 as an eluent, and finally purifyingto obtain a solid desired product M17 (0.85 mmol, yield 85%).

The structure of the desired product M17 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₄₇H₃₃N₃Si, calculated value: 667.87, tested value:667.24.

Elemental analysis: Theoretical value: C 84.52, H 4.98, N 6.29, Si 4.21;tested value: C 84.53, H 4.97, N 6.28, Si 4.22.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 1H), 7.22 (m, 1H), 7.32 (m,2H), 7.36 (m, 9H), 7.43 (m, 1H), 7.48 (m, 3H), 7.54 (m, 6H), 7.58-7.60(m, 4H), 7.66-7.68 (m, 2H), 8.50 (m, 1H), 8.59-8.62 (m, 2H), 8.87 (m,1H).

Example 6

This Example provides an organic compound having the followingstructure:

The method for preparing the organic compound M18 includes the followingsteps:

obtaining intermediate S24 according to the method of steps (1) to (5)in Example 5;

Adding intermediate S24 (1 mmol) and tetramethylethylenediamine (2.5mmol) to 90 mL of THF, reducing the temperature to −78° C. in an ethanolbath, and dropwise adding tert-butyllithium (t-BuLi, 2.5 mmol) into thereaction system within 15 min, and stirring at low temperature for 1 h.Adding S12 (2.5 mmol) at low temperature, and after stirring at lowtemperature for 1 h, naturally returning it to room temperature andstirring overnight. After the reaction was completed, extracting thereaction system with water and ethyl acetate, and then drying theorganic phase over Na₂SO₄. Purifying the crude product by a silica gelcolumn chromatography using a mixed solvent of n-hexane and chloroformin a volume ratio of 5:1 as an eluent, and finally purifying to obtain asolid desired product M18 (0.82 mmol, yield 82%).

The structure of the desired product M18 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₄₁H₂₉N₃Si, calculated value: 591.77, tested value:591.21.

Elemental analysis: Theoretical value: C 83.21, H 4.94, N 7.10, Si 4.75;tested value: C 83.22, H 4.93, N 7.11, Si 4.74.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 1H), 7.22 (m, 1H), 7.32 (m,2H), 7.36 (m, 9H), 7.43 (m, 1H), 7.48 (m, 2H), 7.54 (m, 7H), 7.66-7.68(m, 2H), 8.50 (m, 1H), 8.59-8.62 (m, 2H), 8.91 (m, 1H).

Comparative Example 1

This comparative example provides comparative compound 3, which has thefollowing structure:

the method for preparing the comparative compound 3 includes thefollowing steps:

Under protection of nitrogen, dissolving intermediates S25 (1 mmol) andS3 (2.2 mmol) in 30 mL of toluene, addingtetra(triphenylphosphine)palladium Pd(PPh₃)₄ (0.1 mmol) as a catalyst,and adding 4 mL of aqueous potassium carbonate solution (2 mol/L),refluxing the same for 12 h; after the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, and combining organic phases. Removing all solvents byreduced pressure distillation, and collecting a crude product. Purifyingthe crude product by a silica gel column chromatography using a mixedsolvent of n-hexane and chloroform in a volume ratio of 5:1 as aneluent, and finally purifying to obtain a solid comparative compound 3(0.83 mmol, yield 83%).

The structure of comparative compound 3 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₃₄H₂₂N₄, calculated value: 486.57, tested value:486.18.

Elemental analysis: Theoretical value C 83.93, H 4.56, N 11.51; testedvalue: C 83.91, H 4.57, N 11.52.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.12 (m, 2H), 7.22 (m, 2H), 7.32 (m,4H), 7.48 (m, 4H), 7.55 (m, 2H), 7.66 (m, 2H), 8.50 (m, 2H), 8.59-8.62(m, 4H).

Comparative Example 2

This comparative example provides comparative compound 4, which has thefollowing structure:

the method for preparing the comparative compound 4 includes thefollowing steps:

Under protection of nitrogen, dissolving S26 (1 mmol), S11 (1 mmol) andS27 (1 mmol) in 30 mL of toluene, addingtetrakis(triphenylphosphine)palladium Pd(PPh₃)₄ (0.1 mmol) as acatalyst, and adding 4 mL of aqueous potassium carbonate solution (2mol/L), refluxing same for 12 h; after the reaction was completed,extracting the reaction system with saturated brine and ethyl acetatefor three times, and combining organic phases. Removing all solvents byreduced pressure distillation, and collecting a crude product. Purifyingthe crude product by a silica gel column chromatography using a mixedsolvent of n-hexane and chloroform in a volume ratio of 5:1 as aneluent, and finally purifying to obtain a solid comparative compound 4(0.40 mmol, yield 40%).

The structure of comparative compound 4 was tested: MALDI-TOF-MS (m/z)obtained by Matrix assisted laser desorption ionization time-of-flightmass spectrometry: C₄₂H₃₀N₂Si, calculated value: 590.79, tested value:590.22.

Elemental analysis: Theoretical value: C 85.39, H 5.12, N 4.74, Si 4.75;tested value: C 85.41, H 5.11, N 4.72, Si 4.76.

¹H-NMR (400 MHz, CDCl₃): δ (ppm) 7.22 (m, 1H), 7.32 (m, 2H), 7.36 (m,9H), 7.43 (m, 1H), 7.48 (m, 4H), 7.54 (m, 6H), 7.57-7.61 (m, 4H), 7.68(m, 1H), 8.87 (m, 2H).

The followings are application examples of several organic compoundsused in OLED devices:

Application Example 1

This application example provides an OLED device, which in sequenceincludes: a substrate, an ITO anode, a hole injection layer, a firsthole transport layer, a second hole transport layer, a light emittinglayer, a first electron transport layer, a second electron transportlayer, and a cathode (silver electrode).

The preparation of the OLED device includes the following steps:

(1) cutting the glass substrate into a size of 50 mm×50 mm×0.7 mm,sonicating in acetone, isopropanol and deionized water for 30 minutes,respectively, and then cleaning in ozone for 10 min; mounting theobtained glass substrate with ITO anode to a vacuum depositionapparatus;

(2) vacuum-evaporating the hole injection layer material compound 1 onthe ITO anode layer to a thickness of 5 nm under a vacuum degree of2×10⁻⁶ Pa;

(3) evaporating compound 2 on the hole injection layer as the first holetransport layer to a thickness of 90 nm;

(4) vacuum-evaporating compound 3 on the first hole transport layer as asecond hole transport layer to a thickness of 10 nm;

(5) vacuum-evaporating a light-emitting layer on the second holetransport layer, and the compound 4 was used as a host material of thelight-emitting layer, and compound 5 was used as a doping material ofthe light-emitting layer, the doping ratio was 3% and the thickness was30 nm;

(6) vacuum-evaporating compound 6 on the light-emitting layer as a firstelectron transport layer to a thickness of 5 nm;

(7) vacuum-evaporating the organic compound M16 provided by the presentdisclosure and the doped metal ytterbium (the mass ratio of both is97:3) on the first electron transport layer as a second electrontransport layer with a thickness of 30 nm;

(8) vacuum-evaporating a silver electrode on the second electrontransport layer as a cathode to a thickness of 100 nm.

Application Example 2

This application example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of M19.

Application Example 3

This application example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of M2.

Application Example 4

This application example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of M11.

Application Example 5

This application example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of M17.

Application Example 6

This application example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of M18.

Comparative Example 1

This comparative example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of comparativecompound 1.

Comparative Example 2

This comparative example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of comparativecompound 2.

Comparative Example 3

This comparative example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of comparativecompound 3.

Comparative Example 4

This comparative example differs from the application example 1 in thatM16 in the step (6) is replaced with an equal amount of comparativecompound 4.

Performance Test: (1) Simulation Calculation of Compounds:

Using density functional theory (DFT), for the organic compoundsprovided by the present disclosure, Gaussian 09 program package(Guassian Inc.) was used to optimize and calculate the distributioncondition of molecular frontier orbitals HOMO and LUMO at B3LYP/6-31 G(d) calculation level. At the same time, based on time-dependent densityfunctional theory (TD-DFT), the singlet energy level S₁ and the tripletenergy level T₁ of the compound molecule were simulated and calculated.The results are shown in Table 1.

TABLE 1 Organic HOMO LUMO S1 T₁ E_(g) Examples compounds (eV) (eV) (eV)(eV) (eV) Example 1 M16 5.72 1.64 3.60 2.54 4.08 Example 2 M19 5.74 1.653.54 2.54 4.09 Example 3 M2 5.71 1.59 3.63 2.57 4.12 Example 4 M11 5.671.52 3.65 2.59 4.15 Example 5 M17 5.83 1.59 3.70 2.62 4.24 Example 6 M185.84 1.60 3.63 2.62 4.24 Comparative Comparative 5.98 1.47 3.91 2.724.51 example 1 Compound 1 Comparative Comparative 5.79 1.28 3.86 2.744.51 example 2 Compound 2 Comparative Comparative 5.73 1.84 3.45 2.433.89 example 3 Compound 3 Comparative Comparative 5.96 1.48 3.88 2.714.48 example 4 Compound 4

From the data in Table 1, it can be obtained that the organic compoundS₁ values provided in Examples 1-6 of the present disclosure have noabsorption in the visible light field, and the LUMO (eV) value isbetween 1.4 and 2.0 eV, thus it is suitable to be used as the commonlayer material for electron transport.

(2) Performance Evaluation of OLED Devices:

The current of the OLED device at different voltages was measured with aKeithley 2365A digital nanovoltmeter, and then the current density atdifferent voltages of the OLED device was obtained by dividing thecurrent by the light-emitting area; the OLED device was tested forluminance and radiant energy flux density at different voltages using aKonicaminolta CS-2000 spectroradiometer; according to the currentdensity and luminance of the OLED device at different voltages, workingvoltage V and current efficiency (Cd/A) at the same current density (10mA/cm²) were obtained, Von is the turn-on voltage at a luminance of 1cd/m²; the lifetime T95 was obtained by measuring the time when theluminance of the OLED device reached 95% of the initial luminance (undera test condition of 50 mA/cm²); the test data are shown in Table 2.

TABLE 2 Electron Current Lifetime OLED transport V_(on) V efficiencyLT₉₅ device layer material (V) (V) (Cd/A) (h) Application M16 2.65 3.976.69 68 example 1 Application M19 2.68 3.98 6.62 65 example 2Application M2 2.64 3.92 6.76 70 example 3 Application M11 2.70 4.016.57 63 example 4 Application M17 2.73 4.03 6.46 62 example 5Application M18 2.76 4.05 6.25 63 example 6 Comparative Comparative 2.854.12 5.45 46 example 1 Compound 1 Comparative Comparative 2.82 4.11 5.9147 example 2 Compound 2 Comparative Comparative 2.88 4.15 5.72 49example 3 Compound 3 Comparative Comparative 2.79 4.09 5.82 52 example 4Compound 4

It can be obtained from the data in Table 2 that the OLED deviceprepared based on the organic compounds provided in Examples 1-6 of thepresent disclosure as the material of the electron transport layer has alower turn-on voltage and working voltage, higher current efficiency andlonger working life relative to comparative compound 1, comparativecompound 2, comparative compound 3 and comparative compound 4. Thisbenefits from the molecular structure designed by the present disclosurehaving a multidentate nitrogen-containing ligand and being able tocomplex with metal Yb. Therefore, the heat and electric field generatedduring the device driving process can alleviate the metal movement. Inaddition, among the molecules designed in this application, theo-phenanthroline skeletal structure and a plurality of large stericallyhindered substituents cooperate with each other, so that the organiccompound has a large rigid distortion, and avoids the increase inintermolecular attraction caused by excessive planar structure of theconventional phenanthroline compound. The organic compound has asuitable spatial structure and molecular weight, and its molecularweight is in the range of 600-1200 g/mol, which is helpful forcontrolling the evaporation rate and can suppress the accumulationcaused by the increase in intermolecular attraction. These factors worktogether to reduce the turn-on voltage of the OLED device, reduce theoperating voltage of the OLED device, improve efficiency, and increaselifetime.

Another embodiment of the present disclosure provides an organic lightemitting display device, including the organic light emitting displaypanel as described above.

In the present disclosure, the OLED device may be used in an organiclight emitting display device, and the organic light emitting displaydevice may be a mobile phone display screen, a computer display screen,a television display screen, a smart watch display screen, a smart cardisplay panel, a VR or AR helmet display screen, display screens ofvarious smart devices

Applicant has stated that although an organic compound, an electrontransport material, and an application thereof of the present disclosurehave been described by the above Examples, the present disclosure is notlimited to the above processing steps, that is to say, it is not meantthat the present disclosure has to be implemented depending on the aboveprocessing steps. Any improvements made to the present disclosure,equivalent replacements and addition of adjuvant ingredients to the rawmaterials selected in the present disclosure, and selections of thespecific implementations, all fall within the protection scope and thedisclosure scope of the present disclosure.

What is claimed is:
 1. An organic compound, wherein, the organiccompound has a structure as shown in Formula (I):

wherein, m₁ and m₂ are each independently 0 or 1, and m₁+m₂≥1; U₁ and U₂are each independently selected from any one of the following groups:

X₁, X₂ and X₃ are each independently selected from N or C—H; Y₁ and Y₂are each independently selected from O, S or N—R_(N); R₁, R₂, R₃, R₄ andR₅ are each independently selected from any one of hydrogen, deuterium,tritium, a silicon-containing substituent, a C1-C30 straight or branchedalkyl, a C1-C30 alkoxyl, a substituted or unsubstituted adamantyl, asubstituted or unsubstituted C6-C40 aryl, and a substituted orunsubstituted C3-C40 heteroaryl; when U₁ and U₂ are selected from

at least one of R₁, R₂, R₃, and R₄ is a silicon-containing substituent;when any one of U₁ and U₂ is

at least one of R₁, R₂, R₃, R₄, and R₅ is a silicon-containingsubstituent; R_(U) and R_(N) are each independently selected from anyone of hydrogen, deuterium, tritium, a C1-C30 straight or branchedalkyl, a C1-C30 alkoxyl, a substituted or unsubstituted C6-C40 aryl, anda substituted or unsubstituted C3-C40 heteroaryl; R₁₁ and R₁₂ are eachindependently selected from any one of hydrogen, deuterium, tritium, aC1-C30 straight or branched alkyl, a C1-C30 alkoxyl, a substituted orunsubstituted C6-C40 aryl, and a substituted or unsubstituted C3-C40heteroaryl; u₁, u₄, and u₆ are each independently selected from aninteger of 0-4, u₂ is selected from an integer of 0-6, u₃ and u₅ areeach independently selected from an integer of 0-3; the dotted linerepresents linking position of a group.
 2. The organic compoundaccording to claim 1, wherein, a substituent in the substituted aryl andthe substituted heteroaryl is selected from at least one of deuterium,tritium, a C1-C10 straight or branched alkyl, an adamantyl, a C6-C20aryl, a C3-C20 heteroaryl, a C1-C10 alkoxyl, a C6-C20 arylamino, aC3-C20 cycloalkyl, and a halogen.
 3. The organic compound according toclaim 1, wherein, R₁, R₂, R₃, R₄ and R₅ are each independently selectedfrom any one of hydrogen, deuterium, tritium, a silicon-containingsubstituent, a substituted or unsubstituted C6-C20 aryl, and asubstituted or unsubstituted C3-C20 heteroaryl; when U₁ and U₂ areselected from

at least one of R₁, R₂, R₃, and R₄ is a silicon-containing substituent;when any one of U₁ and U₂ is

at least one of R₁, R₂, R₃, R₄, and R₅ is a silicon-containingsubstituent; when a substituent is present in the above groups, thesubstituent is selected from at least one of deuterium, tritium, aC1-C10 straight or branched alkyl, an adamantyl, a C6-C20 aryl, a C3-C20heteroaryl, a C1-C10 alkoxyl, a C6-C20 arylamino, a C3-C20 cycloalkyl,and a halogen.
 4. The organic compound according to claim 1, wherein, U₁and U₂ are each independently selected from any one of the followinggroups:

wherein, each of R₄, R₅, R_(U), R_(N), R₁₁, R₁₂, u₁, u₂, u₃, u₄, u₅, andu₆ independently has the same limited range as that in claim 1; u₁₁ isan integer of 0-2; the dotted line represents linking position of agroup.
 5. The organic compound according to claim 4, wherein, the U₁ andU₂ are each independently selected from any one of the following groups:

wherein, the dotted line represents linking position of a group.
 6. Theorganic compound according to claim 1, wherein, the organic compound hasa structure as shown in any one of Formula I-1 to Formula I-4:

wherein, each of X₁, X₂, Y₁, Y₂, R₁₁, R₁₁, R₁₂, u₁, u₂, u₃, u₄, u₅, andu₆ independently has the same limited range as that in claim 1; R₁, R₂,R₃, R₄ and R₅ are each independently selected from any one of hydrogen,deuterium, tritium, a silicon-containing substituent, a C1-C30 straightor branched alkyl, a C1-C30 alkoxyl, a substituted or unsubstitutedC6-C40 aryl, and a substituted or unsubstituted C3-C40 heteroaryl; inFormula I-1 and Formula I-2, at least one of R₁, R₂, R₃, and R₄ is asilicon-containing substituent; in Formula I-3 and Formula I-4, at leastone of R₁, R₂, R₃, R₄, and R₅ is a silicon-containing substituent; whena substituent is present in the above groups, the substituent isselected from at least one of deuterium, tritium, a C1-C10 straight orbranched alkyl, an adamantyl, a C6-C20 aryl, a C3-C20 heteroaryl, aC1-C10 alkoxyl, a C6-C20 arylamino, a C3-C20 cycloalkyl, and a halogen.7. The organic compound according to claim 1, wherein, the organiccompound has a structure as shown in any one of Formula I-5 to FormulaI-11:

wherein, each of X₁, X₂, Y₁, Y₂, R_(U), R₁₁, R₁₂, and u₁ independentlyhas the same limited range as that in claim 1; R₁, R₂, R₃, R₄ and R₅ areeach independently selected from any one of hydrogen, deuterium,tritium, a silicon-containing substituent, a C1-C30 straight or branchedalkyl, a C1-C30 alkoxyl, a substituted or unsubstituted C6-C40 aryl, anda substituted or unsubstituted C3-C40 heteroaryl; in Formula I-5,Formula I-6, and Formula I-9, at least one of R₁, R₂, R₃, and R₄ is asilicon-containing substituent; in Formula I-7, Formula I-8, FormulaI-10, and Formula I-11, at least one of R₁, R₂, R₃, R₄, and R₅ is asilicon-containing substituent; when a substituent is present in theabove groups, the substituent is selected from at least one ofdeuterium, tritium, a C1-C10 straight or branched alkyl, an adamantyl, aC6-C20 aryl, a C3-C20 heteroaryl, a C1-C10 alkoxyl, a C6-C20 arylamino,a C3-C20 cycloalkyl, and a halogen.
 8. The organic compound according toclaim 1, wherein, at least one of R₁, R₂ and R₃ is a silicon-containingsubstituent.
 9. The organic compound according to claim 8, wherein, atleast one of R₁ and R₃ is a silicon-containing substituent.
 10. Theorganic compound according to claim 1, wherein the silicon-containingsubstituent has a structure as shown in Formula II:

wherein, Ar is selected from a single bond or a substituted orunsubstituted C6-C30 arylene group; R_(S1), R_(S2) and R_(S3) are eachindependently selected from any one of a C1-C30 straight or branchedalkyl, a C1-C30 alkoxyl, a substituted or unsubstituted C6-C40 aryl, asubstituted or unsubstituted C3-C40 heteroaryl; the dotted linerepresents linking position of a group; when a substituent is present inthe above groups, the substituent is selected from at least one ofdeuterium, tritium, a C1-C10 straight or branched alkyl, an adamantyl, aC6-C20 aryl, a C3-C20 heteroaryl, a C1-C10 alkoxyl, a C6-C20 arylamino,a C3-C20 cycloalkyl, and a halogen.
 11. The organic compound accordingto claim 10, wherein, Ar is selected from a single bond or a C6-C20arylene group.
 12. The organic compound according to claim 10, wherein,R_(S1), R_(S2) and R_(S3) are each independently selected from any oneof a substituted or unsubstituted C6-C40 aryl and a substituted orunsubstituted C3-C40 heteroaryl; when a substituent is present in theabove groups, the substituent is selected from at least one ofdeuterium, tritium, a C1-C10 straight or branched alkyl, an adamantyl, aC6-C20 aryl, a C3-C20 heteroaryl, a C1-C10 alkoxyl, a C6-C20 arylamino,a C3-C20 cycloalkyl, and a halogen.
 13. The organic compound accordingto claim 10, wherein, the silicon-containing substituent is selectedfrom any one of the following groups:

wherein, the dotted line represents linking position of a group.
 14. Theorganic compound according to claim 1, wherein, the organic compound isselected from any one of the following compounds M1 to M41:


15. An electron transport material, wherein, the electron transportmaterial comprises the organic compound according to claim
 1. 16. Theelectron transport material according to claim 15, wherein, the electrontransport material is an electron transport material containing a metal;and the metal is selected from any one or a combination of at least twoof an alkali metal, an alkali metal compound, an alkaline earth metal,an alkaline earth metal compound, a transition metal, a transition metalcompound, a rare earth metal, and a rare earth metal compound.
 17. Adisplay panel, the display panel may be used as a display device,wherein, the display panel comprises an OLED device, the OLED devicecomprises an anode, a cathode, and an organic thin film layer betweenthe anode and the cathode, and the organic thin film layer comprises anelectron transport layer; the material of the electron transport layerincludes the electron transport material according to claim
 15. 18. Thedisplay panel according to claim 17, wherein, the organic thin filmlayer further comprises an electron injection layer; material of theelectron injection layer includes the electron transport materialaccording to claim 15.